Cubebol is a compound found in nature, namely in cubeb oil which is isolated from berries of Piper cubeba, or true cubebs. A compound having a similar structure (see discussion below) is found in species of cubebs known as "false cubebs", which are not well defined and can comprise several species of Piper. The oil of true cubebs has long since been known in the flavor industry, but its use is strictly limited to a number of "exotic" applications, for example the flavoring of spicy sauces and bitter alcohols, or "bitters". This is due to the characteristic bitter, piquant and pungent flavor of the oil, which, as a result, does not lend itself to large-scale use in the flavor industry.
Cubeb oil is a complex mixture of around fifty compounds (see N. B. Shankaracharya et al, Pafai Journal Jan.-Mar. 1995, pp. 33-39). One constituent amongst these compounds which is well defined is the aforementioned cubebol, which has already been referred to in works dating from the 1950s and relating to the flavor and fragrance industry, for example in Guenther, The Essential Oils, Vol. II (1952). At that time, the structure of cubebol had not yet been clarified, and the name "cubebol" was used for a product extracted from false cubebs, while the oil of true cubebs yielded a product known as "cubeb camphor". The aforementioned work by Guenther, for example, refers on page 287 to a compound by the name of cubebol isolated from the oil of "false" cubebs and said not to be identical to a compound by the name of "cubeb camphor", isolated from the oil of true cubebs.
According to more recent work on cubebol, the two compounds are, with a fair amount of probability, the same (see F. Vanasek et al, Coll. Czech. Chem. Comm. 1960 (25), p. 919 and A. Tanaka et al, J. Chem. Soc. Perkin 1., 1972, p. 1721), although the identity of these two compounds has not actually been proved. From this point on, the name cubebol will be used to designate the compound of the formula (I) hereinabove which is isolated from the oil of true cubebs.
It is very surprising that cubebol has never been used in the flavor industry, despite the fact that cubebol and cubeb camphor have long been known, as is reflected in the work by Guenther, which states on page 287: "Cubebol as such is not used in our industry." This has remained the case until now.
A very current topic in the flavor industry is the search for molecules which have a delayed and prolonged refreshing effect when they come into contact with the mucous membranes of the mouth. This is due to the fact that a large number of compounds, in particular derivatives of (-)-menthol, are already known which have a pronounced refreshing effect developing rapidly in the oral cavity and lasting for around 10 to 15 minutes at the most. However, refreshing agents which have a longer-lasting effect are desired. Despite all the effort invested by chemists in the synthesis of new chemical substances or in structural modifications to compounds with a known refreshing effect (see e.g. applications DE-A-26 08 226, EP-A-507 190 and EP-A-583 651 filed by Haarmann & Reimer GmbH, and application PCT/IB98/01821 filed on 16.11.98 by the applicant), they have not succeeded in developing or finding substances having the desired quality of a long-lasting refreshing effect.